Download PDF
Synfacts 2007(2): 0124-0124  
DOI: 10.1055/s-2006-955756
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Amurensinine

Contributor(s): Philip Kocienski, Thomas Snaddon
U. K. Tambar, D. C. Ebner, B. M. Stoltz*
California Institute of Technology, Pasadena, USA
Further Information

Publication History

Publication Date:
23 January 2007 (online)

    Permissions and Reprints

Significance

(+)-Amurensinine is an isopavine alkaloid. The members of this family contain a bis-benzannulated azabicyclo[3.2.2]nonane core and are of interest for the treatment of various neurological disorders. Noteworthy in this synthesis are (1) the regioselective 1,5-C-H insertion of a Rh carbenoid, (2) an interesting ring expansion by acyl alkylation of an aryne, and (3) the Pd-catalyzed oxidative kinetic resolution of a secondary alcohol.